organic compounds

 = 0.10 mm1
T = 296 K

Acta Crystallographica Section E

Structure Reports
Online

0.40  0.35  0.30 mm

Data collection

ISSN 1600-5368

4-Fluoro-N-[(E)-3,4,5-trimethoxybenzylidene]aniline

5699 measured reflections
3358 independent reflections
2468 reflections with I > 2(I)
Rint = 0.017

Bruker Kappa APEXII CCD
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
Tmin = 0.962, Tmax = 0.971

Refinement

R. K. Balachandar,a S. Kalainathan,a Shibu M. Eappenb and
Jiban Podderc*
a

Centre for Crystal Growth, School of Advanced sciences, VIT University, Vellore
632 014, India, bSophisticated Test and Instrumentation Centre (STIC), Cochin
University PO, Cochin 682 022, Kerala, India, and cDepartment of Physics,
Bangladesh University of Engineering and Technology, Dhaka 1000, Bangladesh
Correspondence e-mail: jpodder@phy.buet.ac.bd
Received 5 June 2013; accepted 27 June 2013
˚;
Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.003 A
R factor = 0.040; wR factor = 0.128; data-to-parameter ratio = 17.7.

R[F 2 > 2(F 2)] = 0.040
wR(F 2) = 0.128
S = 1.00
3358 reflections
190 parameters

1 restraint
H-atom parameters constrained
˚ 3 
max = 0.14 e A
˚ 3 
min = 0.13 e A

Table 1
˚ ,  ).
Hydrogen-bond geometry (A
D—H  A

D—H

H  A

D  A

D—H  A

C4—H4  N1i
C7—H7  O3ii

0.93
0.93

2.57
2.58

3.492 (3)
3.504 (3)

174
173

Symmetry codes: (i) x þ 1; y þ 12; z þ 1; (ii) x þ 1; y þ 12; z þ 2.

The title compound, C16H16FNO3, exists in a trans configura˚ ]. The central
tion with respect to the C N bond [1.258 (2) A
methoxy O atom deviates from the plane of the attached
˚ . The dihedral angle between
benzene ring by 0.0911 (14) A
the aromatic rings is 47.58 (11) . The crystal structure features
C—H  N and C—H  O interactions.

Related literature
For the uses and biological importance of Schiff base
¨ nver et
compounds, see: Xia et al. (2009); Shah et al. (1992); U
al. (2004). For related structures, see: Fun et al. (2011); Khalaji
& Simpson (2009); Balachandar et al. (2013).

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2
and SAINT (Bruker, 2004); data reduction: SAINT and XPREP
(Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare
et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia,
2012); software used to prepare material for publication: SHELXL97
and PLATON (Spek, 2009).

The authors acknowledge the STIC, Cochin, for the singlecrystal XRD facility. They also thank Mr P. Narayanan and Dr
K. Sethusankar, RKM Vivekananda College (Autonomous),
Chennai 600 004, and VIT University Management for
providing the research facilities.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: DS2233).

References

Experimental
Crystal data
C16H16FNO3
Mr = 289.30
Monoclinic, P21
˚
a = 7.1147 (9) A
˚
b = 8.3841 (9) A

o1234

Balachandar et al.

˚
c = 12.9217 (13) A 
= 105.266 (5)
˚3
V = 743.59 (14) A
Z=2
Mo K radiation

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl.
Cryst. 26, 343–350.
Balachandar, R. K., Kalainathan, S., Eappen, S. M. & Podder, J. (2013). Acta
Cryst. E69, o905.
Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc.,
Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011). Acta Cryst. E67, o1273–
o1274.
Khalaji, A. D. & Simpson, J. (2009). Acta Cryst. E65, o553.
Shah, S., Vyas, R. & Mehta, R. H. (1992). J. Indian Chem. Soc. 69, 590–590.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
¨ nver, H., Karakas, A. & Elmali, A. (2004). J. Mol. Struct. 702, 49–54.
U
Xia, D.-G., Ye, Y.-F. & Lei, K.-W. (2009). Acta Cryst. E65, o3168.

doi:10.1107/S1600536813017741

Acta Cryst. (2013). E69, o1234

indicating a typical imine double bond.. Moreover. 2004).supplementary materials supplementary materials Acta Cryst. Then filtering. software used to prepare material for publication: SHELXL97 (Sheldrick. They are known to exibit potent anti-bacterial. o1234 sup-1 . During the diffraction experiment.x. 1993).258 (2) Å is shorter than the N–C bond [1.4. The symmetry codes: (i). In addition to that. The flurine atom F1 is deviated from the phenyl ring (C1–C6) by -0. o1234 [doi:10. 1 .5-trimethoxybenzylidene]aniline R. 2012). exists in a trans configuration with respect to the C═N bond [1. 2004). Balachandar. The dihedral angle formed between the phenyl rings (C1–C6) and (C8–C13) is 47. 2008). The crystal packing is stabilized by C4—H4···N1i and C7—H7···O3ii inter-molecular interactions. S.258 (2) Å]. successful application of Schiff bases requires a careful study of their characteristics. K.z. program(s) used to refine structure: SHELXL97 (Sheldrick.58 (11) °.5Ueq(C) for methyl group.x. (2013). One of the oxygen atom attached to the phenyl ring (C8–C13) is deviated from the same plane by -0. the C–N–C angle is 118. Eappen and Jiban Podder Comment Schiff bases are among the most useful ligands in coordination chemistry as they readily form stable complexes with most transition metals (Xia et al.4.2Ueq(C) for aryl atoms.1/2 + y. 0. The H atoms bound to the C atoms were treated as riding atoms.93 (17) °. molecular graphics: ORTEP-3 for Windows (Farrugia. antiinflammatory and anti-cancer activities (Shah et al. E69.196 g) and 4-Fluoroaniline (1 mmol. E69. d(C–H) = 0.0911 (14) Å. 998 Friedel pairs were merged.z. X-ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. which were taken in equimolar ratio and dissolved in methanol (20 ml). 2004). Refinement The positions of hydrogen atoms were localized from the difference electron density maps and their distances were geometrically constrained.1107/S1600536813017741] 4-Fluoro-N-[(E)-3. data reduction: SAINT and XPREP (Bruker. (ii).411 (3) Å]. Therefore. Kalainathan. 2009). program(s) used to solve structure: SIR92 (Altomare et al. (2013)..0243 (23) Å..172 g).1 . anti-convulsant. 2004). After 4 days.5-trimethoxybenzaldehyde (1 mmol. 2009). The resulting mixture was stirred at room temperature for overnight. The rotation angles for methyl group is optimized by least squares. it shows the Non-linear optical properties (Ünver et al.1/2 + y. C16 H16 F N O3.2 . colourless single crystals were obtained using methanol as solvent by keeping the solution for slow evaporation suitable for single-crystal X-ray structure analysis. Experimental The title compound was prepared by the condensation reaction between of 3. Shibu M. The N1═C8 bond length of 1. 0.93 Å and Uiso(H) = 1. Acta Cryst. drying the synthesized compound dissolved in a 20 ml of methanol to purify the title material by recrystallization process at least for three times. cell refinement: APEX2 and SAINT (Bruker. 2008) and PLATON (Spek. 1 . 1. 1992). Computing details Data collection: APEX2 (Bruker. The title compound. with d(C–H) = 0..96 Å and Uiso(H) = 1.

9–28.3841 (9) Å c = 12.40 × 0. o1234 F(000) = 304 Dx = 1. showing C4—H4···N1i and C7—H7···O3ii intermolecular interactions.4. colourless 0. P21 Hall symbol: P 2yb a = 7.10 mm−1 T = 296 K Block. Figure 2 The crystal packing of the title compound. E69.supplementary materials Figure 1 The molecular structure of the title compound with the atom numbering scheme. displacement ellipaoids are drawn at 30% probability level.30 mm sup-2 .3° µ = 0.9217 (13) Å β = 105.292 Mg m−3 Mo Kα radiation. λ = 0.5-trimethoxybenzylidene]aniline Crystal data C16H16FNO3 Mr = 289. The H atoms not involved in the bonding have been excluded for clarity.71073 Å Cell parameters from 2468 reflections θ = 2. H atoms are present as small spheres of arbitary radius. viewed down a-axis. 4-Fluoro-N-[(E)-3.1147 (9) Å b = 8.59 (14) Å3 Z=2 Acta Cryst.35 × 0.266 (5)° V = 743.30 Monoclinic. (2013).

's in cell parameters are only used when they are defined by crystal symmetry. and is not relevant to the choice of reflections for refinement.supplementary materials Data collection Bruker Kappa APEXII CCD diffractometer Radiation source: fine-focus sealed tube Graphite monochromator ω and φ scan Absorption correction: multi-scan (SADABS.0465 (4) 0.0745 (5) 0. angles and torsion angles.001 Δρmax = 0.4108 (4) 0.'s are taken into account individually in the estimation of e. in the dihedral angle between two l.0273 (2) 0.0763 (7) 0.6458 (2) 0.s.s.6764 (5) 0.128 S = 1.0596 (4) 0.3532 (3) 0.1847 (2) 0.s. An approximate (isotropic) treatment of cell e.d.0800 (2) 0. The weighted R-factor wR and goodness of fit S are based on F2.3531 (2) 0.96978 (16) 0. and R.d.5225 (3) 0. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) F1 N1 O3 C4 H4 O5 O6 C3 C2 H2 C6 C7 H7 C8 C13 H13 C11 x y z Uiso*/Ueq 0.0795 0.d.3987 0.1191 (7) 0.2598 0.6724 0.3137 0.8696 (5) 0.s.056* 0.'s in distances.971 5699 measured reflections 3358 independent reflections 2468 reflections with I > 2σ(I) Rint = 0.65551 (15) 0.70169 (14) 1. correlations between e.0053 0. with F set to zero for negative F2. E69. planes.088* 0.0557 (4) 0.4548 0.14 e Å−3 Δρmin = −0.040 wR(F2) = 0.4394 (3) 0.'s involving l. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc.9942 (4) 0.factors based on ALL data will be even larger.5185 (4) 0.5447 0.2770 (2) −0.5810 −0.80220 (16) 0. The cell e.5155 (2) 0.4847 (3) 0.s.13 e Å−3 Special details Geometry.0474 (4) 0.'s (except the e. θmin = 2. o1234 sup-3 .3977 (3) 0.d. All e. 1999) Tmin = 0.1708 (3) 0. Bruker.0659 (2) 0.3°.057* 0.5751 (3) 0. Refinement.s.1984 (2) 0.0737 (7) 0.2666 (2) 0.9455 (4) 1.5003 (3) 0.d. Refinement of F2 against ALL reflections.13224 (11) 0.962.108* 0.s.d.0530 (5) 0.017 θmax = 28.017P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.12728 (18) 0.'s is used for estimating e.0453 (4) 0.00 3358 reflections 190 parameters 1 restraint Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ2(Fo2) + (0. R-factors based on F2 are statistically about twice as large as those based on F.8430 0.02505 (12) 0.81378 (13) 1.6199 (3) 0.5578 (2) 0. planes) are estimated using the full covariance matrix.0279 (2) 0.s. (2013).85798 (15) 0.0482 (4) Acta Cryst.6295 −0.9° h = −6→9 k = −11→11 l = −17→16 Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.96847 (15) 1.05790 (17) 0. Tmax = 0.0767P)2 + 0.51013 (17) 0.s.0901 (9) 0.0608 (4) 0. conventional R-factors R are based on F.6363 0.d.

0016 (8) −0.0258 (3) −0.1116 (12) 0.0697 (10) 0.0411 0.384 (3) 1.119* 0.1114 (4) −0.093* 0.0448 (10) 0.0139 (10) 0.0710 (15) 0.3294 0.0794 (7) 0.0468 (4) 0.0531 (11) 0.0522 (10) 0.5338 0.1259 (17) 0.1283 (3) −0.0110 (8) 0.2671 1.0562 (11) 0.0558 (11) 0.0170 (14) 0.096 (2) 0.1819 −0.119* 0.0074 (8) 0.7021 (2) 0.258 (2) C8—C13 C8—C9 1.0548 (8) 0.4166 0.0099 (14) 0.0777 (7) 0.0546 (11) 0.359 (3) 1.1824 0.0330 (17) −0.0667 (9) 0.6864 0.0142 (2) −0.0754 (11) 0.0073 (7) 0.5085 (4) 0.6632 1.0456 (10) 0.073* 0.0481 (10) 0.0049 (9) 0.388 (3) sup-4 .0943 (4) −0.0638 (11) 0.0540 (11) 0.0028 (8) 0.0111 (12) 0.0620 (14) −0.0614 (13) 0.0727 (16) 0.5502 (4) 0.129* 0.0585 (9) 0.7564 1.0630 (14) 0.0827 0.supplementary materials C1 H1 C12 C15 H15A H15B H15C C5 H5 C9 H9 C10 C14 H14A H14B H14C C16 H16A H16B H16C 0.062* 0.0355 (17) 0.0697 (9) 0.103 (2) 0.0010 (8) 0.143* 0.80236 (17) 0.0019 (8) 0.0018 (13) 0.0605 (6) 0.0513 (5) 0.0039 (8) 0.0048 (9) 0.129* Atomic displacement parameters (Å2) F1 N1 O3 C4 O5 O6 C3 C2 C6 C7 C8 C13 C11 C1 C12 C15 C5 C9 C10 C14 C16 U11 U22 U33 U12 U13 U23 0.1824 0.0784 (10) 0.0031 (8) 0.0847 0. E69.56337 (18) 0.0858 (18) 0.0014 (9) −0.0256 (17) −0.0027 (9) 0.0009 (8) 0.1612 −0.0071 (8) 0.0014 (7) 0.0406 (10) 0.0425 (9) 0.0379 (9) 0.115 (3) 0.0385 (14) 0. º) F1—C3 N1—C7 Acta Cryst.097 (2) 0.2205 (4) 0.02398 (15) 1.0955 (10) 0.8184 (3) 0.0437 (2) 1.3258 (3) −0.0030 (8) 0.0863 (8) 0.0111 (9) 0.0654 (15) 0.0550 (8) 0.4435 (4) 0.0363 (9) 0.0093 (11) 0.0696 (4) −0.0012 (9) −0.0454 (10) 0.0019 (8) −0.9763 1.0506 (12) 0.69503 (18) 0.0791 (15) 0.0179 (7) 0.4532 0.1691 1.2132 0.8679 0.0396 −0.0526 (10) 0.097 (2) 0.0088 (14) −0.1440 (16) 0.0434 (15) 0.143* 0.0123 (15) 0.6812 0.0033 (8) −0.119* 0.0488 0.0458 (8) 0.0681 (16) 0.0136 (7) 0.143* 0.0029 (7) 0.0345 (9) 0.0022 (8) −0.1639 −0.1788 −0.0164 (10) 0. (2013).0216 (18) −0.0650 (12) 0.0838 0.1811 0.0658 (15) 0.0010 (8) 0.0007 (8) −0.0501 (9) 0.0619 (14) 0.0766 (12) 0.0513 (5) 0.0847 (18) 0.1214 (2) 0.0191 (13) −0.1201 0.0864 (19) 0.6291 0.0647 (13) 0.0543 (12) 0.129* 0. o1234 1.102 (2) 0.0266 (12) 0.0511 (10) 0.0016 (16) 0.0128 0.4905 0.0699 (14) 0.0071 (13) −0.0132 (14) Geometric parameters (Å.0007 (14) 0.2415 (3) 0.0117 (7) 0.0018 (12) 0.1925 (2) 1.0927 (2) 0.113 (2) 0.0416 (9) 0.0378 (10) 0.0053 (7) −0.0364 (9) 0.2774 0.0290 (9) −0.0319 (15) −0.0077 (8) 0.0437 (10) 0.85863 (16) 0.7281 0.0125 (9) 0.2145 0.0047 (8) 0.0057 (10) 0.0097 (8) 0.099 (2) 0.5116 0.0552 0.3381 (3) 0.0283 (15) 0.0948 0.0608 (10) 0.0445 (10) 0.0330 (12) −0.0049 (6) 0.0129 (7) 0.

6 (3) 119.4 124.60 (16) 121.370 (4) 0.359 (2) 1.384 (2) 1.366 (2) 1.13 (17) 109.9300 0.3 118.0 121.5 109.9300 0.9600 0.375 (3) 0.73 (17) 121.5 109.386 (3) 0.9600 0.9300 1.2 O6—C12—C13 O6—C12—C11 C13—C12—C11 O3—C15—H15A O3—C15—H15B H15A—C15—H15B O3—C15—H15C H15A—C15—H15C H15B—C15—H15C C4—C5—C6 C4—C5—H5 C6—C5—H5 C10—C9—C8 C10—C9—H9 C8—C9—H9 O5—C10—C9 O5—C10—C11 C9—C10—C11 O5—C14—H14A O5—C14—H14B H14A—C14—H14B O5—C14—H14C H14A—C14—H14C H14B—C14—H14C O6—C16—H16A O6—C16—H16B H16A—C16—H16B O6—C16—H16C H16A—C16—H16C H16B—C16—H16C 125.9600 0.28 (18) 120.409 (3) 1.5 109.36 (17) 118.5 109.0 117.412 (3) 1.8 (2) 118.9600 C7—N1—C6 C11—O3—C15 C3—C4—C5 C3—C4—H4 C5—C4—H4 C10—O5—C14 C12—O6—C16 C4—C3—C2 C4—C3—F1 C2—C3—F1 C3—C2—C1 C3—C2—H2 C1—C2—H2 C1—C6—C5 C1—C6—N1 C5—C6—N1 N1—C7—C8 N1—C7—H7 C8—C7—H7 C13—C8—C9 C13—C8—C7 C9—C8—C7 C12—C13—C8 C12—C13—H13 C8—C13—H13 O3—C11—C12 O3—C11—C10 C12—C11—C10 C6—C1—C2 C6—C1—H1 C2—C1—H1 118.18 (19) 117.81 (17) 122.5 (2) 119.7 (2) 123.9300 1.347 (4) 1.5 109.411 (3) 1.5 109.351 (4) 1.9300 1.9600 0.392 (3) 0.5 109.93 (17) 113.98 (18) 114.9600 0.21 (16) 119.9 120.4 120.85 (16) 119.2 119. (2013).supplementary materials N1—C6 O3—C11 O3—C15 C4—C3 C4—C5 C4—H4 O5—C10 O5—C14 O6—C12 O6—C16 C3—C2 C2—C1 C2—H2 C6—C1 C6—C5 C7—C8 C7—H7 1.78 (16) 120.9600 0.375 (3) 1.5 109.9600 0.455 (3) 0.75 (17) 119.09 (17) 114.9 (3) 118.5 109.362 (2) 1.5 109.5 109.378 (3) 0.9 (2) 123.75 (18) 120.9300 1.7 119.0 (2) 120. o1234 sup-5 .42 (17) 119.9 119.5 109.5 120.5 109.03 (17) 120.419 (3) 1.5 109.5 Acta Cryst.9300 C13—C12 C13—H13 C11—C12 C11—C10 C1—H1 C15—H15A C15—H15B C15—H15C C5—H5 C9—C10 C9—H9 C14—H14A C14—H14B C14—H14C C16—H16A C16—H16B C16—H16C 1.3 (3) 117.9600 0.5 109.28 (19) 118.5 109.9 (2) 121. E69.50 (17) 118.5 120.5 118.7 119.388 (3) 1.3 120.27 (17) 109.

492 (3) 3. −z+1. −z+2. º) D—H···A i C4—H4···N1 C7—H7···O3ii D—H H···A D···A D—H···A 0.58 3. y+1/2.supplementary materials Hydrogen-bond geometry (Å. Acta Cryst. o1234 sup-6 . (2013).57 2. y+1/2.93 2.504 (3) 174 173 Symmetry codes: (i) −x+1.93 0. E69. (ii) −x+1.

58 D···A 3. (2013). −z+1. y+1/2. o1234 sup-6 . º) D—H···A C4—H4···N1 C7—H7···O3ii i D—H 0. (ii) −x+1.93 0.93 H···A 2.supplementary materials Hydrogen-bond geometry (Å. E69. Acta Cryst. y+1/2.492 (3) 3.57 2. −z+2.504 (3) D—H···A 174 173 Symmetry codes: (i) −x+1.